US2298078A - Plastic masses similar to factice and linoxyn - Google Patents
Plastic masses similar to factice and linoxyn Download PDFInfo
- Publication number
- US2298078A US2298078A US288593A US28859339A US2298078A US 2298078 A US2298078 A US 2298078A US 288593 A US288593 A US 288593A US 28859339 A US28859339 A US 28859339A US 2298078 A US2298078 A US 2298078A
- Authority
- US
- United States
- Prior art keywords
- factice
- linoxyn
- vinyl
- tall oil
- plastic masses
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920003023 plastic Polymers 0.000 title description 7
- 239000004033 plastic Substances 0.000 title description 7
- 239000003784 tall oil Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- -1 glycerine ester Chemical class 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 3
- SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 229960000834 vinyl ether Drugs 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- HJBDUKOSCLGKRS-UHFFFAOYSA-N 1,1-bis(ethenoxy)octadecane Chemical compound CCCCCCCCCCCCCCCCCC(OC=C)OC=C HJBDUKOSCLGKRS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- MJCYPBSRKLJZTB-UHFFFAOYSA-N trifluoroborane;dihydrate Chemical compound O.O.FB(F)F MJCYPBSRKLJZTB-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
Definitions
- the present invention relates to interpolymerisation products of vinyl ethers having a plurality of vinyl groups inthe molecule and esters of saturated alcohols with tall oil.
- interpolymerisation products capable of wide use are obtained by polymerising tall oil esterified, with saturated alcohols in admixture with vinyl ethers having a plurality of vinyl groups in the molecule, and if desired with further vinyl compounds.
- tall oil esters of a great variety of saturated alcohols as for example from esters of monohydric alcohols, such as methyl, ethyl, butyl, lauryl or benzyl alcohol, or of polyhydric alcohols, such as the glycols and polyglycols or glycerine, trimethylol ethane or propane, hexanetriol, and also from mixed esters of tall oil, a polybasic carboxylic acid such as succinic or phthalic acid and a polyhydric alcohol which already have resinous properties, or from thickened tall oil esters of saturated alcohols.
- the thickened tall oil esters may be obtained from tall oil esters by the action of heat, if desired in the presence of oxygen or compounds yielding oxygen or of acid-reacting condensing agents, as for example boron fluoride.
- Suitable vinyl ethers having a plurality of vinyl groups in the molecule are for example glycol and polyglycoldivinyl ethers or octadecanediol divinyl ether.
- the interpolymerisation may be carried out in the manner usual for polymerisation reactions,
- .masses similar to factice or linoxyn They are suitable for the purposes for which factice or linoxyn are used, inparticular as binding agents for floor covering masses or as additions to rubber instead of factice.
- Example 1 To a mixture of 12.7 parts of tall oil glycerine ester, 4.7 parts of diethylene glycol divinyl ether, 28 parts of vinyl ethyl ether, parts of vinyl methyl ether and 8.7 parts of a resin obtained by condensation of equomolecular amounts of colophony and maleic anhydride and subsequent esteriflcation with glycerine, there is added at about 10 C. such an amount of a 5 per cent solution of boron fluoride dihydrate in dioxane that noticeable polymerisation takes place.
- a part of the vinyl methyl ether takes no part in the polymerisation and serves merely as a diluent and also, by boiling under reflux, as an agent for regulating the temperature.
- the polymerisation mixture may be kept constant at about 9 C;
- the finished interpolymerisation product in which only about 46 parts of polymerised vinyl methyl ether are contained, is a brown, friable, elastic mass similar to linoxyn.
- the product when blown with oxygen or oxygen-containing gases, such as air, becomes more plastic and may then be added with greater amounts of flllers than without such an aftertreatment.
- Plastic masses similar to factice and iinoxyn 3. Plastic masses similar to factice and linoxyn comprising interpolymerisation products of at least, a vinyl ether having a plurality of vinyl groups in the molecule and of the glycerine ester of tall oil.
- Plastic masses similar to factice and linoxyn comprising interpolymerisation products of glycol divinyl ethers and of esters of saturated al.- cohols with tall oil.
- Plastic masses similar to factice and linoxyn comprising an interpolymerisation product of tall oil glycerine ester, diethylene glycol divinyl ether and at least one vinyl ether of a monohydric aliphatic alcohol.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2298078X | 1938-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2298078A true US2298078A (en) | 1942-10-06 |
Family
ID=7994087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US288593A Expired - Lifetime US2298078A (en) | 1938-08-15 | 1939-08-05 | Plastic masses similar to factice and linoxyn |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2298078A (fr) |
| FR (1) | FR858464A (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439377A (en) * | 1948-04-13 | Utilization of tall oil | ||
| US2482086A (en) * | 1944-04-01 | 1949-09-20 | Westinghouse Electric Corp | Resinous compositions and use thereof in forming electrical members and laminated products |
| US2555834A (en) * | 1947-04-25 | 1951-06-05 | Gen Mills Inc | Copolymers of fatty oils and polyallyl ethers |
| US2603612A (en) * | 1947-12-29 | 1952-07-15 | Elissabide Rene Jean Benjamin | Fabric treating thermoplastic resin-rosin composition |
-
1939
- 1939-07-28 FR FR858464D patent/FR858464A/fr not_active Expired
- 1939-08-05 US US288593A patent/US2298078A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439377A (en) * | 1948-04-13 | Utilization of tall oil | ||
| US2482086A (en) * | 1944-04-01 | 1949-09-20 | Westinghouse Electric Corp | Resinous compositions and use thereof in forming electrical members and laminated products |
| US2555834A (en) * | 1947-04-25 | 1951-06-05 | Gen Mills Inc | Copolymers of fatty oils and polyallyl ethers |
| US2603612A (en) * | 1947-12-29 | 1952-07-15 | Elissabide Rene Jean Benjamin | Fabric treating thermoplastic resin-rosin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| FR858464A (fr) | 1940-11-26 |
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